Open AccessCobalt-Catalyzed Benzylic Borylation: Enabling Polyborylation and Functionalization of Remote, Unactivated C(sp3)–H Bonds
Author(s) -
W. Neil Palmer,
Jennifer V. Obligacion,
Iraklis Pappas,
Paul J. Chirik
Publication year - 2016
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.5b12249
Subject(s) - borylation , chemistry , isomerization , cobalt , catalysis , diimine , alkyl , toluene , boron , medicinal chemistry , carboxylate , photochemistry , surface modification , polymer chemistry , stereochemistry , organic chemistry , aryl
Cobalt dialkyl and bis(carboxylate) complexes bearing α-diimine ligands have been synthesized and demonstrated as active for the C(sp(3))-H borylation of a range of substituted alkyl arenes using B2Pin2 (Pin = pinacolate) as the boron source. At longer reaction times, rare examples of polyborylation were observed, and in the case of toluene, all three benzylic C-H positions were functionalized. Coupling benzylic C-H activation with alkyl isomerization enabled a base-metal-catalyzed method for the borylation of remote, unactivated C(sp(3))-H bonds.